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Peroxides as “Switches” of Dialkyl H‑Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2‑Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates

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posted on 05.09.2014, 00:00 by Xiao-Lan Chen, Xu Li, Ling-Bo Qu, Yu-Chun Tang, Wen-Peng Mai, Dong-Hui Wei, Wen-Zhu Bi, Li-Kun Duan, Kai Sun, Jian-Yu Chen, Dian-Dian Ke, Yu-Fen Zhao
Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The dialkyl H-phosphonate (RO)2P­(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)2POH. TBHP triggered α-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C2-acylation of benzothiazoles and C2-phosphonation of benzothiazoles.